ethyl (3aR,4S,5S,7aS)-5,7a-dihydroxy-4-methyl-1-oxo-3a,5-dihydro-3H-2-benzofuran-4-carboxylate | 144066-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: ethyl (3aR,4S,5S,7aS)-5,7a-dihydroxy-4-methyl-1-oxo-3a,5-dihydro-3H-2-benzofuran-4-carboxylate
• CAS: 144066-90-0
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: QIKAYGZUKLKRGY-OSTYVCCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (3aR,4S,5S,7aS)-5,7a-dihydroxy-4-methyl-1-oxo-3a,5-dihydro-3H-2-benzofuran-4-carboxylate 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (3aS,4S,5R,7aR)-5,7a-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Synthesis of a fully functionalized CD ring system of taxol

  摘要：

  与紫杉醇 CD 环系统相关的关键构件 16 和 17 已通过立体控制的高效序列以外消旋形式合成，该序列具有新颖的 Diels-Alder 反应和氧杂环丁烷形成。

  DOI：

  10.1039/c39920001118
• 作为产物：
  描述：

  ethyl (E)-2-methyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enoate 在 对甲苯磺酸 、 苯硼酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 66.0h， 生成 ethyl (3aR,4S,5S,7aS)-5,7a-dihydroxy-4-methyl-1-oxo-3a,5-dihydro-3H-2-benzofuran-4-carboxylate
  参考文献：
  名称：

  Total Synthesis of taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system

  摘要：

  A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

  DOI：

  10.1021/ja00107a007

文献信息

• Synthesis of a fully functionalized CD ring system of taxol
  作者：K. C. Nicolaou、J. J. Liu、C.-K. Hwang、W.-M. Dai、R. K. Guy

  DOI：10.1039/c39920001118

  日期：——

  Key building blocks 16 and 17 related to taxol CD ring system have been synthesized in racemic form via a stereocontrolled and efficient sequence featuring a novel Diels–Alder reaction and oxetane formation.

  与紫杉醇 CD 环系统相关的关键构件 16 和 17 已通过立体控制的高效序列以外消旋形式合成，该序列具有新颖的 Diels-Alder 反应和氧杂环丁烷形成。
• Total Synthesis of taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system
  作者：K. C. Nicolaou、J.-J. Liu、Z. Yang、H. Ueno、E. J. Sorensen、C. F. Claiborne、R. K. Guy、C.-K. Hwang、M. Nakada、P. G. Nantermet

  DOI：10.1021/ja00107a007

  日期：1995.1

  A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.